Classifications

• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
  • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
  • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
  • A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
  • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings

Definitions

• the present invention relates to a plant disease controlling composition and a method for controlling a plant disease.
• An object of the present invention is to provide a composition having an excellent control effect on a plant disease .
• the present inventors have intensively studied to find out a composition having an excellent control effect on a plant disease. As a result, they have found that a composition comprising a compound represented by the formula (1) and one or more inorganic fungicidal compound selected from the following group (A) shows a synergistic activity, and thus has an excellent control effect on a plant disease, and therefore the present invention has been completed .
• the present invention provides:
• a plant disease controlling composition comprising a compound represented by the formula (1) :
• group (A) a group consisting of fludioxonil, pencycuron, ametoctradin, chloroneb, chlorothalonil , oxine-copper , cyflufenamid, dichlofluanid, dicloran, diethofencarb, dinocap, dithianon, edifenphos, fenaminosulf, fentin, fluazinam, fluoroimide, flusulfamide , flutianil, fosetyl-Al, hydrargaphen, iprobenfos, metrafenon, milneb, penflufen, phosdiphen, phthalide, prothiocarb, pyrazophos, sedaxane, silthiofam, spiroxamine, tebufloquin, and tolyfluanid.
• a method for controlling a plant disease which comprises applying each effective amount of the compound of the formula ( 1 ) :
• group (A) a group consisting of fludioxonil, pencycuron, ametoctradin, chloroneb, chlorothalonil , oxine-copper, cyflufenamid, dichlofluanid, dicloran, diethofencarb, dinocap, dithianon, edifenphos, fenaminosulf, fentin, fluazinam, fluoroimide, flusulfamide, flutianil, fosetyl-Al, hydrargaphen, iprobenfos, metrafenon, milneb, penflufen, phosdiphen, phthalide, prothiocarb, pyrazophos, sedaxane, silthiofam, spiroxamine, tebufloguin, and tolyfluoride, a group consisting of fludioxonil, pencycuron, ametoctradin, chloroneb, chloro
• group (A) for controlling a plant disease
• group (A) a group consisting of fludioxonil, pencycuron, ametoctradin, chloroneb, chlorothalonil, oxine-copper, cyflufenamid, dichlofluanid, dicloran, diethofencarb, dinocap, dithianon, edifenphos, fenaminosulf, fentin, fluazinam, fluoroimide, flusulfamide, flutianil, fosetyl-Al, hydrargaphen, iprobenfos, metrafenon, milneb, penflufen, phosdiphen, phthalide, prothiocarb, pyrazophos, sedaxane, silthiofam, spiroxamine, tebufloquin, and tolyfluanid.
• the present invention enables to control a plant disease .
• a plant disease controlling composition of the present invention (hereinafter, referred to as a composition of the present invention) comprises a compound represented by the formula (1) :
• an amide compound of the present invention and one or more inorganic compound selected from the following group (A) (hereinafter, referred to as a inorganic compound of the present invention) ,
• group (A) a group consisting of fludioxonil, pencycuron, ametoctradin, chloroneb, chlorothalonil , oxine-copper, cyflufenamid, dichlofluanid, dicloran, diethofencarb, dinocap, dithianon, edifenphos, fenaminosulf, fentin, fluazinam, fluoroimide, flusulfamide, flutianil, fosetyl-Al, hydrargaphen, iprobenfos, metrafenon, milneb, penflufen, phosdiphen, phthalide, prothiocarb, pyrazophos, sedaxane, silthiofam, spiroxamine, tebufloquin, and tolyfluanid.
• the present amide compounds are those described in for example, WO 95/27693 pamphlet and WO 02/10101 pamphlet, and thus can be prepared according to the method described therein.
• the present amide compound has one asymmetric carbon.
• a compound represented by the formula (1) wherein an enantiomer having R- absolute configuration is enriched is referred to as the amide compound having R- absolute configuration .
• the present amide compound encompasses the following compounds :
• Fludioxonil, pencycuron, chloroneb, chlorothalonil, oxine-copper, cyflufenamid, dichlofluanid, dicloran, diethofencarb, dinocap, dithianon, edifenphos, fenaminosulf, fentin, fluazinam, fluoroimide, flusulfamide, flutianil, fosetyl-Al, iprobenfos, metrafenon, milneb, phosdiphen, phthalide, prothiocarb, pyrazophos, silthiofam, spiroxamine, and tolyfluanid are described in for example, ''The PESTICIDE MANUAL - 15th EDITION (BCPC published) ISBN 1901396188'', pages 520, 871, 150, 197, 852, 261, 328, 345, 351, 388, 402, 417, 1231, 491, 513, 537
• Hydrargaphen is a compound of CAS No. 14235-86-0. These compounds are either commercially available, or can be prepared by a known method.
• composition of the present invention may be a mixture as itself of the present amide compound and the present inorganic compound
• the composition of the present invention is usually prepared by mixing the present amide compound, the present inorganic compound and an inert carrier, and if necessary, adding a surfactant or other pharmaceutical additives, and then formulating into the form of oil solution, emulsifiable concentrate, flowable formulation, wettable powder, granulated wettable powder, dust formulation, granules and so on.
• Such formulations can be used by itself or with an addition of other inert components as an agent for controlling a plant disease.
• the composition of the present invention can contain 0.1 to 99 % by weight, preferably 0.2 to 90 % by weight, and more preferably 1 to 80 % by weight of the present amide compound and the present inorganic compound in total.
• Examples of a solid carrier used on the formulation include finely-divided power or particles of clay consisting of minerals (e.g., kaolin clay, attapulgite clay, bentonite, montmorillonite, acid clay, pyrophyllite, talc, diatomaceous earth, or calcite) , natural organic substances (e.g., corncob powder, or walnut shell powder), synthetic organic substances (e.g., urea), salts (e.g., calcium carbonate, or ammonium sulfate) , synthetic inorganic substances (e.g., synthetic hydrous silicon oxide) and so on.
• minerals e.g., kaolin clay, attapulgite clay, bentonite, montmorillonite, acid clay, pyrophyllite, talc, diatomaceous earth, or calcite
• natural organic substances e.g., corncob powder, or walnut shell powder
• synthetic organic substances e.g., urea
• salts
• liquid carrier examples include aromatic hydrocarbons (e.g., xylene, alkyl benzene, or methylnaphtalene) , alcohols (e.g., 2-propanol, ethylene glycol, propylene glycol, or ethylene glycol monoethyl ether), ketones (e.g., acetone, cyclohexanone, or isophorone) , vegetable oils (e.g., soybean oil, or cotton oils), petroleum-derived aliphatic hydrocarbons, esters, dimethylsulfoxide, acetonitrile and water.
• aromatic hydrocarbons e.g., xylene, alkyl benzene, or methylnaphtalene
• alcohols e.g., 2-propanol, ethylene glycol, propylene glycol, or ethylene glycol monoethyl ether
• ketones e.g., acetone, cyclohexanone, or isophorone
• surfactant examples include anionic surfactant (e.g., alkyl sulfate salts, alkylaryl sulfate salts, dialkyl sulfosuccinate salts, polyoxyethylene alkylaryl ether phosphates, lignin sulfonate, or naphthalenesulfonate formaldehyde polycondensation) , nonionic surfactant (e.g., polyoxyethylene alkylaryl ether, polyoxyethylene alkyl polyoxypropylene block copolymer, or sorbitan fatty acid ester) and cationic surfactant (e.g., alkyltrimethyl ammonium salts) .
• anionic surfactant e.g., alkyl sulfate salts, alkylaryl sulfate salts, dialkyl sulfosuccinate salts, polyoxyethylene alkylaryl ether phosphates, lignin sulfonate,
• water-soluble polymer e.g., polyvinyl alcohol, or polyvinyl pyrrolidone
• polysaccharides e.g. arabic gum, alginic acid and salts thereof, CMC (carboxymethyl- cellulose) , or xanthan gum
• inorganic substances e.g, aluminum magnesium silicate, or alumina-sol
• antiseptic agent coloring agent
• PAP isopropyl acid phosphate
• stabilizing agent e.g., BHT
• composition of the present invention can also be prepared by separately formulating the present amide compound and the present inorganic compound into different formulations by the above procedures, if necessary, further diluting each of them with water, thereafter, mixing the separately prepared different formulations or the dilute solutions .
• composition of the present invention may further contain one or more other fungicide and/or insecticide.
• composition of the present invention is used to control a plant disease by applying it to a plant or a soil for cultivating the plant.
• the plant disease which can be controlled by the present invention is exemplified below:
• Rice diseases blast (Magnaporthe oryzae) , helminthosporium leaf spot (Cochliobolus miyabeanus) , sheath blight ⁇ Rhizoctonia solani) and bakanae disease ⁇ Gibberella fuj ikuroi) ;
• Citrus diseases melanose (Diaporthe citri) , scab (Elsinoe fawcetti) and Penicillium rot (Penicillium digitatum, P. i tali cum) ;
• Apple diseases blossom blight ⁇ Monilinia mali) , canker ⁇ Valsa ceratosperma) , powdery mildew (Podosphaera leucotricha) , Alternaria leaf spot (Alternaria alternata apple pathotype) , scab (Venturia inaequalis) , bitter rot (Colletotrichum acutatum) and late blight (Phytophtora cactorum) ;
• Pear diseases scab ⁇ Venturia nashicola, V. pirina) , black spot (Alternaria alternate Japanese pear pathotype) , rust (Gymnosporangium haraeanum) and late blight (Phytophtora cactorum) ;
• Grapes diseases anthracnose (Elsinoe ampelina) , ripe rot (Glomerella cingulata) , powdery mildew (Uncinula necator) , rust (Phakopsora ampelopsidis) , black rot (Guignardia bidwellii) , downy mildew (Plasmopara viticola) and Gray mold (Botrytis cinerea) ;
• anthracnose (Colletotrichum lagenarium) , powdery mildew (Sphaerotheca fuliginea) , gummy stem blight (Mycosphaerella melonis) , Fusarium wilt (Fusarium oxysporum) , downy mildew ( Pseudoperonospora cubensis) , Phytophthora rot ( Phytophthora sp. ) and damping-off (Pythium sp.) ;
• Tomato diseases early blight ⁇ Alternaria solani) , leaf mold (Cladosporium fulvum) and late blight (Phytophthora infestans) ;
• Egg plant disease brown spot (Phomopsis vexans) and powdery mildew (Erysiphe cichoracearum) ;
• Alternaria leaf spot Alternaria japonica
• white spot Cercosporella brassicae
• clubroot Pierroot
• Lasmodiophora brassicae clubroot
• downy mildew Peronospora parasitica
• Rapeseed diseases Sclerotinia rot (Sclerotinia sclerotiorum) , black spot (Alternaria brassicae) , powdery mildew (Erysiphe cichoracearum) , blackleg (Leptosphaeria maculans) ;
• Soybean diseases purple seed stain (Cercospora kikuchii) , Sphaceloma scad (Elsinoe glycines) , pod and stem blight (Diaporthe phaseolorum var. sojae) , rust (Phakopsora pachyrhizi) and phytophthora stem rot (Phytophthora sojae) ;
• Adzuki-bean diseases Gray mold (Botrytis cinerea) , Sclerotinia rot (Sclerotinia sclerotiorum) ;
• Peanut diseases leaf spot (Cercospora personata) , brown leaf spot (Cercospora arachidicola) and southern blight (Sclerotium rolfsii) ;
• Plant pea diseases powdery mildew (Erysiphe pisi) ; Potato diseases: early blight (Alternaria solani) and late blight (Phytophthora infestans) ;
• Tea diseases net blister blight (Exobasidium reticulatum) , white scab (Elsinoe leucospila) , gray blight (Pestalotiopsis sp.) and anthracnose (Colletotrichum theae-sinensis) ;
• Cotton diseases fusarium wilt (Fusarium oxysporum) , damping-off (Rhizoctonia solani) ;
• Tabacco diseases brown spot (Alternaria longipes) , powdery mildew (Erysiphe cichoracearum) , anthracnose (Colletotrichum tabacum) , downy mildew (Peronospora tabacina) and late blight (Phytophthora nicotianae) ;
• Rose diseases black spot (Diplocarpon rosae) and powdery mildew (Sphaerotheca pannosa) ;
• Chrysanthemum diseases leaf blight (Septoria chrysanthemi-indici) and white rust ( Puccinia horiana) ;
• Turfgrass diseases dollar spot ⁇ Sclerotinia homeocarpa) , brown patch and large patch ⁇ Rhizoctonia solani) ;
• Banana diseases Sigatoka disease ⁇ Mycosphaerella fijiensis, Mycosphaerella musicola, Pseudocercospora musae) .
• Crops corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, adzuki-bean, kindney bean, peanut, buckwheat, beet, rapeseed, sunflower, sugar cane, and tobacco, etc.;
• Vegetables solanaceous vegetables (eggplant, tomato, pimento, pepper, and potato, etc.) , cucurbitaceous vegetables (cucumber, pumpkin, zucchini, water melon, melon, and squash, etc.) , cruciferous vegetables (Japanese radish, white turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, leaf mustard, broccoli, and cauliflower, etc.
• asteraceous vegetables (burdock, crown daisy, artichoke, and lettuce, etc.) , liliaceous vegetables (green onion, onion, garlic, and asparagus) , ammiaceous vegetables (carrot, parsley, celery, and parsnip, etc.) , chenopodiaceous vegetables (spinach, and Swiss chard, etc.) , lamiaceous vegetables (Perilla frutescens, mint, and basil, etc.) , strawberry, sweet potato, Dioscorea japonica, and colocasia, etc.;
• Fruits pomaceous fruits (apple, pear, Japanese pear, Chinese quince, and quince, etc. ) , stone fleshy fruits (peach, plum, nectarine, Prunus mume, cherry fruit, apricot and prune, etc.) , citrus fruits (Citrus unshiu, orange, lemon, lime, and grapefruit, etc.) , nuts (chestnut, walnuts, hazelnuts, almond, pistachio, cashew nuts, and macadamia nuts, etc.) , berrys (blueberry, cranberry, blackberry, and raspberry, etc.) , grape, kaki fruit, olive Japanese plum, banana, coffee, date palm, and coconuts, etc. ; and
• Trees other than fruit trees tea, mulberry, flowering plant, roadside trees (ash, birch, dogwood, Eucalyptus, Ginkgo biloba, lilac, maple, Quercus, poplar, Judas tree, Liquidambar formosana, plane tree, zelkova, Japanese arborvitae, fir wood, hemlock, juniper, Pinus, Picea, and Taxus cuspidate), etc.
• plants include plants which resistance has been imparted by genetic recombination.
• the method for controlling a plant disease of the present invention (hereinafter, referred to as the method for controlling of the present invention) is carried out by applying each effective amount of the present amide compound and the present inorganic compound to the plants or the soil for cultivating the plant.
• Such the plants may be, for example, foliages of plant, seeds of plant, or bulbs of plant.
• the bulbs herein are intended to mean bulb, corm, rootstock, tubera, tuberous root and rhizophore.
• the present amide compound and the present inorganic compound may be applied separately around the same time to the plant or the soil for cultivating the plant, but is usually applied as the composition of the present invention in terms of a convenience on applying.
• examples of the method of applying the present amide compound and the inorganic compound include foliage treatment, soil treatment, root treatment and seed treatment .
• Such the foliage treatment includes for example, a method of applying the composition of the present invention to a surface of the plant to be cultivated by a foliage application or a stem application.
• Such the root treatment includes for example, a method of soaking a whole or a root of the plant into a medicinal solution comprising the present amide compound and the present inorganic compound, and a method of attaching a solid formulation comprising the present amide compound, the present inorganic compound and the solid carrier to a root of the plant.
• Such the soil treatment includes for example, soil broadcast, soil incorporation, and irrigation of the medicinal solution to a soil.
• Such the seed treatment includes for example, an applying of the composition of the present invention to a seed or a bulb of the plant to be prevented from the plant disease, specifically, for example, a spray treatment by spraying a suspension of the composition of the present invention in a mist form to a surface of a seed or a surface of a bulb, a smear treatment by smearing the wettable powder, the emulsifiable concentrate or the flowable formulation of the composition of the present invention with added by small amounts of water or as itself to a seed or a bulb, an immerse treatment of a seed into a solution of the composition of the present invention for a given time, a film-coating treatment, and a pellet-coating treatment .
• a spray treatment by spraying a suspension of the composition of the present invention in a mist form to a surface of a seed or a surface of a bulb
• a smear treatment by smearing the wettable powder
• Each dose of the present amide compound and the present inorganic compound in the method for controlling of the present invention may be varied depending on a kind of plant to be treated, a kind or a frequency of an occurrence of a plant disease as a control subject, a dosage form, a treatment period, a treatment method, a treatment site, a climate condition, etc.
• a total amount of the present amide compound and the inorganic compound is usually 1 to 500 g, preferably 2 to 200 g, and more preferably 10 to 100 g, per 1000 m 2 .
• Each dose of the present amide compound and the present inorganic compound in the treatment for seed is usually 0.001 to 10 g, and preferably 0.01 to 1 g, per 1kg of seeds.
• the emulsifiable concentrate, the wettable powder or the flowable formulation, etc. is usually applied by diluting them with water, and then spreading them.
• each concentration of the present amide compound and the present inorganic compound contain 0.0005 to 2% by weight, and preferably 0.005 to 1% by weight of the present amide compound and the present inorganic compound in total.
• the dust formulation or the granular formulation, etc, is usually applied as itself without diluting them.
• test examples are given below.
• a testing solution prepared by mixing the flowable formulation of the present compound (racemate) prepared by the above procedure and a commercial wettable powder of fludioxonil or chlorothalonil to a predetermined concentration to treat the leaf disk.
• conidium of gray mold fungus ⁇ Botrytis cinerea is suspended into potato dextrose broth (DIFCO) in a density of about 10 5 conidium/mL and is then subjected to a spray inoculation. After leaving to stand the leaf disk in a growth chamber set up at 15°C for four days, an onset area on the leaf is measured and then calculated an onset area rate (hereinafter, referred to as an onset area rate of treated group) .
• DIFCO potato dextrose broth
• onset area rate of non-treated group 20 micro liter water instead of 20 micro liter a testing medicine solution to calculate an onset area rate (hereinafter, referred to an onset area rate of non-treated group) .
• a preventive value is calculated from the above onset area rate of treated group and the onset area rate of non- treated group by the following equation:
• Test Example 1 The same operations as described in Test Example 1 are carried out with cyflufenamid, diethofencarb, dithianon, fluazinam, flusulfamide, fosetyl-Al, metrafenon, penflufen, phthalide, sedaxane, spiroxamine or tebufloquin, instead of fludioxonil or chlorothalonil, so as to calculate respective preventive values.
• testing medicine solution is substituted with a predetermined concentration of each dimethyl sulfoxide solution of the present compound (racemate) , cyflufenamid, diethofencarb, dithianon, fluazinam, flusulfamide, fosetyl- Al, metrafenon, penflufen, phthalide, sedaxane, spiroxamine or tebufloquin, so as to calculate respective preventive values .
• Test Example 1 For comparison, the same operations as described in Test Example 1 are carried out with the exception that the testing medicine solution is substituted with a predetermined concentration of each dimethyl sulfoxide solution of fludioxonil or chlorothalonil , so as to calculate a preventive value.

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• Life Sciences & Earth Sciences (AREA)
• Dentistry (AREA)
• Wood Science & Technology (AREA)
• Plant Pathology (AREA)
• Health & Medical Sciences (AREA)
• Engineering & Computer Science (AREA)
• Agronomy & Crop Science (AREA)
• General Health & Medical Sciences (AREA)
• Environmental Sciences (AREA)
• Zoology (AREA)
• Pest Control & Pesticides (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Pretreatment Of Seeds And Plants (AREA)
• Chemical & Material Sciences (AREA)
• Inorganic Chemistry (AREA)

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